NUCLEOPHILIC ADDITIONS TO 4-SUBSTITUTED SNOUTANONES - GETTING A MEASURE OF LONG-RANGE ELECTROSTATIC AND ORBITAL CONTROL OF PI-FACE SELECTIVITY

Authors
MEHTA G RAVIKRISHNA C KALYANARAMAN P CHANDRASEKHAR J
Citation
G. Mehta et al., NUCLEOPHILIC ADDITIONS TO 4-SUBSTITUTED SNOUTANONES - GETTING A MEASURE OF LONG-RANGE ELECTROSTATIC AND ORBITAL CONTROL OF PI-FACE SELECTIVITY, Journal of the Chemical Society. Perkin transactions. I (Print), (12), 1998, pp. 1895-1897
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I (Print) → ACNP
ISSN journal
0300922X
Issue
12
Year of publication
1998
Pages
1895 - 1897
Database
ISI
SICI code
0300-922X(1998):12<1895:NAT4S->2.0.ZU;2-F
Abstract
Pentacyclic ketones 10a-e (snoutan-9-ones) undergo nucleophilic additi ons with the same facial preference as the corresponding norsnoutanone s 9a-e, but with markedly reduced selectivity, revealing the involveme nt of electrostatic effects in the former and implying the importance of hyperconjugative orbital interactions in determining pi-face select ivity in the latter systems.